The three general schemes to polyhydroxylated pyrrolizidines outlined could be used for the synthesis of many Senecio alkaloids like otonecine and for the nonquinoid portion of mitomycin C. One tact will define and utilize the effect of nitrogen on ketone enolate functionalization. A second ploy uses new activated cyclopropanes in cyclooctanones and conversion of these ketones into otonecine-like structures.